By John P. Richard (Eds.)
Advances in actual natural Chemistry offers the chemical neighborhood with authoritative and important tests of the numerous elements of actual natural chemistry. the sector is a quickly constructing one, with effects and methodologies discovering program from biology to reliable country physics. * stories the appliance of quantitative and mathematical tools in the direction of realizing chemical difficulties * Multidisciplinary volumes hide natural, organometallic, bioorganic, enzymes and fabrics themes
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Thus the (four) points for protonation of a double bond with a terminal methylene group fall below the correlation line but show a steeper slope. 9, after correction for the statistical effect of six equivalent hydrogens in the isopropyl cation. 1. 0 for formation of the 1-butene, based on the equilibrium constant for isomerization of the alkenes. 0 respectively. 1 log units more positive than the value derived from protonation of propene directly. In its favor, protonation of 2-butene occurs at a ‘‘secondary’’ rather than (as for 2-propene) a ‘‘primary’’ vinylic carbon atom, as is also true of formation of the cations correlated in Fig.
Measurements are also available for methyl benzoate,138,142 for which the protonated ester and hydrate adduct are intermediates in acid-catalyzed ester hydrolysis. 144 Comparisons of structurally related hydroxy- and methoxy-substituted cations show that hydroxy is more stabilizing by between 4 and 5 log units. 130 It seems clear that the explanation of these differences lies in the advantage in solvation energy conferred by an OH group attached to a charge center. 138 Other examples of the superior solvation of OH relative to MeO groups conjugated with a positive charge are mentioned below (p.
However, as described below (p. 57) the diffusion method has been used to infer a pKa for the protonation of a quinone methide. Oxygen substituent effects on arenonium ions It is also possible to examine the effect of oxygen substituents on the stability of arenonium ions. 152,153 The tautomeric constants may be combined with pKas for protonation of the keto tautomer and ionization of the phenol to provide pKas for protonation of the aromatic ring of phenol and the phenoxide ion. As illustrated in Scheme 18 the unstable keto tautomer of phenol 22 was produced by photolysis of the bicyclooctene dione 21.